1,2-Dichloroethane → tert-Butyl 2-(4-chlorophenyl)-3-(4-{[(3-methoxy-3-oxopropyl)amino]carbonyl}phenyl)hexanoate

HRID 2408159Notes

Reaction equation

HRID 2408159 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH:7]([CH:15]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)[CH2:16][CH2:17][CH3:18])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:43][O:44][C:45](=[O:49])[CH2:46][CH2:47][NH2:48].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH:7]([CH:15]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([NH:48][CH2:47][CH2:46][C:45]([O:44][CH3:43])=[O:49])=[O:24])=[CH:26][CH:27]=2)[CH2:16][CH2:17][CH3:18])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:28])=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 192794Methyl beta-alanateHCID 58553821HCID 58553821, compound

Product 1

HCID 86660371tert-Butyl 2-(4-chlorophenyl)-3-(4-{[(3-methoxy-3-oxopropyl)amino]carbonyl}phenyl)hexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the product from Step A (6.2 g, 15.3 mmol), EDC (4.4 g, 23.0 mmol), and HOBt (3.1 g, 23.0 mmol) in anhydrous DCM (200 mL) was stirred for 30 min at RT, then β-alanine methyl ester (2.1 g, 15.3 mmol) and DIEA (8.0 mL, 45.9 mmol) were added. After being stirred for 12 hours at RT, the mixture was diluted with DCM then washed with 100 mL of 0.5 M HCl (aq) then 100 mL of saturated NaCl (aq). The organic layer was dried over Na2SO4, filtered, then concentrated. The major diastereomer of the title compound was obtained by trituration with hexane.

Workup

  1. stirringAfter being stirred for 12 hours at RT
  2. washthen washed with 100 mL of 0.5 M HCl (aq)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8947013ba76a43e1b2e4ed7333e30116
Source dataset
uspto-grants-2014_08
Patent number
US08809579B2

Reaction notes

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